Nitrile alkylations through sulfinyl-metal exchange

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Abstract

Triple alkylation: Phenylsulfinyl- and phenylthioacetonitrile can function as trianion equivalents of acetonitrile by sequential alkylation and sulfinyl-metal exchange (see scheme; mCPBA=meta-chloroperoxybenzoic acid). The metalated nitriles alkylate a range of electrophiles to obtain nitriles with quaternary centers. The sulfinyl-metal exchange proceeds under very mild conditions and has a high functional-group tolerance. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Nath, D., & Fleming, F. F. (2011). Nitrile alkylations through sulfinyl-metal exchange. Angewandte Chemie - International Edition, 50(49), 11790–11793. https://doi.org/10.1002/anie.201105630

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